Phenol halogen phthalein compound.



No Drawing.

tetrachlorphthalein,

UNITED sTAtrns arana: OFFICE.

WILLIAM R. ORNDORFF, F ITHACA, NEW YORK, ASSIGNOR T0 PARKE, DAVIS & COM- PANY, OF DETROIT, MICHIGAN, A CORPORATION OF MICHIGAN.

Specification of Letters Patent.

PHENOL HALOGEN PHTHALEIN COMPOUND.

atented Nov. 2,1909.

Application filed. April 22,1909. Serial No. 491,542. (Specimens) all whom it may concern:

'Be it known that I, \VILLIAM ll. Oun- -nonrr, a citizen of the United States of -.ments in Phenol Halogen lhthalein Com-- pounds. of which the following is a specification.

The invention relates to a new class of compounds, which I have termed phenol I halogen phthaleins, and consists in the new chemical substance and in the process of manufacturing the same. The new body is a, derivative of a phenol and a halogen phthalicacid, and is characterized by its laxative and purgative properties,and certain physical properties, as will be hereina'fter described.

For the purpose of illustration, a specific compound in the class mentioncd,preferably a tetrachlorin derivative of phenol phthalein,-which I have named phenol will be described. This substance has the following formula:

c, n cno,

- or structurally expressed:

mixture solidifies. When the reaction is completed, the mass is treated with a large excess of water, and steam is passed into the lnixt-uie. The crude phenol tetrachltnphthalein is then filtered oti', washed with hot water, and dissolved preferably in a. ten per cent. solution of sodium hydroxid. The alkaline solution is tiltercthto remove a small amount of totrachlortluoran termed as'a by-product, and hydrochloric or sul- 'turic acid is added in excess to precipitate the phenol tetrachlorphthalein, which is then filtered otr, washed thoroughly with water. and dried. The reaction is repre-.

sentod by the following equation:

' c,n,on

CO CO a i +HQO 'lheoretically, 100 grams of tetrachlorby recrystallization from methyl or ethylalcohols, using bone black to decolorize the solution, or it may be recrystallized from other solvents as acetone, ether, or acetic acid.

The new compound possesses valuable purgative or laxative properties, and the following physical characteristics: it is a colorless, crystalline body, the crystals being substantially rectangular plates soluble in Warm ethyl alcohol, acetone, ether, glacial acetic acid, and in certain oils as olive oil, slightly soluble in chloroform and benzene, and in soluble in water and ligroin. In concentrat'ed sulfuric acid it dissolves easily in the cold with a reddish yellow color, and is precipitated unchanged from this solution by water. It darkens slightly at ap proximately 308 (3., and melts with de composition at approximately 316 C. when heated in a sealed capillary tube. It dissolves readily in solutions of potassium, sodium and ammonium hydroxide or of the carbonates of the alkali metals, forming colored solutions of the salts. In concentrated alkaline solutions the color is red, in thin layers purplefwhilo in dilute solutions it is violet-red. "In very dilute alkaline solutions the color has a bluish tint, chich distinguishes it from phenol phthulein. The addition of acids tothe violet-red alkaline solution decolorizes it at once, and precipitates the colorless phenol tetrachlorphthalcin. The addition of a large excess of the caustic alkalies to the violet-red dilute alkaline solution of the compound decolorizes it on standing, probably owing to the formation of the tripotassium or sodium salt of the carbinol carbonic acid. vVhen administered by the mouth or hypodermically, it acts as previously stated as a valuable purgative or laxative.

The term acid in the specification and claims is used in its broad sense, and coinprehends the acid proper or its anhydrid,

either of which with the other ingredients described Will produce the desired compound.

Whatl claim as my invention is,- l. The liei-enrdescribed process of 't'ornrmg phenol halogenphthaleins, consisting in subjecting a phenol and a halogen phthalic acid to the action of heat while in the pres (1166 of a dehydrating agent.

2. The herein-described process of ,iorming phenol halogen phthaleins, which consists in heating a phenol and a halogen phthalic acid in the presence oi? a dehydrating agent until solidification of the mixture takes place.

3. The herein-described process of formlug plamol halogen phthalcins, which consists in heating curbolic acid and tetra-chlorphthulic acid in the presence of a dehydrating agent and maintaining the heat at a high temperature until solidification of the mixture takes place.

4. A laxative compound, derived from a phenol and a halogen phthulic acid, characterized by its laxative action and the following physical properties: It is a colorless,

tasteless and odorless crystalline body, soluble in methyl alcohol, acetone and ether, and

insoluble in water; it dissolves in solutions of the alkalies, and is precipitated from these solutions by acids, and melts at approximately 316 C. when heated in a closed capillary tube.

lowing physical properties: It is a colorless,

tastele, 5 and odorless crystalline body, soluble in methyl and ethyl alcohols, acetone, ether, glacial acetic acid, and insoluble in water and ligroin, it dissolves in solutions of the alkalies oralkaline carbonates, and is precipitated from these solutions by acids, and melts at approximately 316 0. when heated in a sealed capillary tube.

6. The herein-described compound, derived from carbolic acid and tetrachlorpl'ithalic acid, characterized by its laxative-and purgative action, whichis a colorless crystalline body without taste or odor, melts at approximately 316 C. when heated in a sealed capillary tube, is soluble in methyl and ethyl alcohols, acetone, ether, and glacial acetic acid, and insoluble in Water and ligroin, it dissolves in solutions of the alkalies or alkaline carbonates with a red color, and is precipitated from these solutions by acids, and dissolves in the cold in concentrated sulfuric acid with a reddish yellow color, and is precipitated unchanged from this solution by water. i

l n testimony whereof I affix my signature in presence of two witnesses.

' W'JTLLIAM R. ()RNDORFF.

Witnesses 'l. G, .Dnnnmnon, E, H. Nionons. 

